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Citric Acid → (RS)-2-methyl-4-methylidene-3-ethyl-2-cyclopenten-1-yl (1R)-trans-3-(2,2-dichloro-vinyl)-2,2-dimethylcyclopropanecarboxylate

HRID 1379934
ノート
印刷プレビュー

反応式

HRID 1379934 の反応式
[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[CH3:13][C:14]1[CH:15]([OH:22])[CH2:16][C:17](=[CH2:21])[C:18]=1[CH2:19][CH3:20].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@@H:6]([C:7]([O:22][CH:15]2[CH2:16][C:17](=[CH2:21])[C:18]([CH2:19][CH3:20])=[C:14]2[CH3:13])=[O:8])[C:5]1([CH3:11])[CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 311Citric AcidHCID 1049PyridineHCID 6454308(1R,3S)-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chlorideHCID 15389976(RS)-2-methyl-4-methylidene-3-ethylcyclopent-2-en-1-ol

生成物 1

HCID 15389982(RS)-2-methyl-4-methylidene-3-ethyl-2-cyclopenten-1-yl (1R)-trans-3-(2,2-dichloro-vinyl)-2,2-dimethylcyclopropanecarboxylate収率 86.3%

試薬・触媒・溶媒 2

HCID 314042,6-Di-tert-butyl-4-methylphenol触媒HCID 1140Toluene溶媒

実験手順

625 mg of (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid chloride was added under ice-water cooling to a mixed solution of 400 mg of (RS)-2-methyl-4-methylidene-3-ethylcyclopent-2-en-1-ol, 5 mg of 2,6-di-t-butyl-4-methylphenol and 274 mg of pyridine in 6 ml of toluene. The reaction was continued at an ambient temperature for eight hours. The reaction solution was added to a 5% citric acid solution under ice-water cooling, and extracted three times with diethyl ether. The combined ether layer was washed successively with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography to yield 781 mg of (RS)-2-methyl-4-methylidene-3-ethyl-2-cyclopenten-1-yl (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (Compound No.5). Yield 82%. (Eluent: n-hexane/ethyl acetate=30/1, 2,6-di-t-butyl-4-methylphenol 0.1%) nD23 1.5251

後処理

  1. extractionextracted three times with diethyl ether
  2. washThe combined ether layer was washed successively with a saturated sodium hydrogencarbonate solution
  3. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-f112712c5f5b4fe0afb7363dcc802169
出典データセット
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05672779

反応ノート

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